Acetic acid, 2-(4-formylphenoxy)- → HCID 178514004, compound

HRID 592086Notes

Reaction equation

HRID 592086 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH:21]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][CH:24]=1)=O>>[C:17]([C@H:11]1[C@H:12]2[CH2:16][C@H:15]([CH:14]=[CH:13]2)[C@H:10]1[NH:9][C:6]1[C:5]([Cl:20])=[CH:4][N:3]=[C:2]2[NH:1][C:21]([C:23]3[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][CH:24]=3)=[N:8][C:7]=12)(=[O:18])[NH2:19]

Participants

3

Reactant 2

HCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178514004HCID 178514004, compoundYield 29%

Procedure

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1 eq.) and 2-(4-Formylphenoxy)acetic acid (53) (1.1 eq) were reacted in an analogous manner as compound CCXXIII to yield the desired product (29%) as a white solid. NMR: δ (1H, 400 MHz, DMSO-d6): 1.37 (1H, d, J=8.4 Hz), 2.23 (1H, d, J=8.4 Hz), 2.62 (1H, d, J=7.6 Hz), 2.77 (1H, s), 2.88 (1H, s), 4.31 (2H, bs), 5.20 (1H, t, J=8.8 Hz), 6.34-6.41 (2H, m), 6.77 (1H, d, J=8.8 Hz), 6.95 (2H, d, J=8 Hz), 7.07 (1H, d, J=8.8 Hz), 7.20-7.25 (1H, m), 7.75 (1H, bs), 7.90 (1H, s), 8.02 (2H, d, J=8.0 Hz).

Sources & evidence

ORD record
ord-768987479b024dbba60aecd832efaba4
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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